Diethyl Ether → 2,2-Di(benzylthiomethyl)pentanal

HRID 1197365Notes

Reaction equation

[CH2:1]([S:8][CH2:9][C:10]([CH2:16][S:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:13][CH2:14][CH3:15])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].C(OCC)C>ClCCl>[CH2:18]([S:17][CH2:16][C:10]([CH2:9][S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH2:13][CH2:14][CH3:15])[CH:11]=[O:12])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 2,2-di-(benzylthiomethyl)pentan-1-ol (1.0 g Example XI) in dry dichloromethane (10 ml) was added to a stirred suspension of pyridinium chlorochromate (1.8 g) and anhydrous sodium acetate (0.11 g) in dry dichloromethane (25 ml) at 0° C., under a current of nitrogen. The reaction mixture was allowed to warm to 20° C. and then stirred for 2 hours. Dry diethyl ether was added and the mixture stirred for 30 minutes. The ethereal extracts were decanted off and the residue was washed with further portions of diethyl ether. The combined ethereal extracts were dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. The residue was purified by chromatography on a mixture of silica and charcoal, eluting with diethyl ether. 2,2-Di(benzylthiomethyl)pentanal was obtained as a pale yellow oil (0.27 g).

Workup

stirringthe mixture stirred for 30 minutes
customThe ethereal extracts were decanted off
washthe residue was washed with further portions of diethyl ether
dry with materialThe combined ethereal extracts were dried over anhydrous magnesium sulphate
customthe solvent was removed in vacuo
customThe residue was purified by chromatography on a mixture of silica and charcoal
washeluting with diethyl ether

Sources & evidence

ORD record: ord-c1be3119c75c4806b7c90e1cdbd135f4
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116862

Reaction notes

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